WO2008074709A1 - Dérivés d'anthraquinone en tant que marqueurs pour liquides - Google Patents

Dérivés d'anthraquinone en tant que marqueurs pour liquides Download PDF

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Publication number
WO2008074709A1
WO2008074709A1 PCT/EP2007/063813 EP2007063813W WO2008074709A1 WO 2008074709 A1 WO2008074709 A1 WO 2008074709A1 EP 2007063813 W EP2007063813 W EP 2007063813W WO 2008074709 A1 WO2008074709 A1 WO 2008074709A1
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Prior art keywords
liquid
general formula
alkyl
aryl
compounds
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PCT/EP2007/063813
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German (de)
English (en)
Inventor
Rüdiger Sens
Thomas Gessner
Sophia Ebert
Christos Vamvakaris
Wolfgang Ahlers
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Basf Se
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Application filed by Basf Se filed Critical Basf Se
Priority to AU2007336381A priority Critical patent/AU2007336381A1/en
Priority to BRPI0706749-6A priority patent/BRPI0706749A2/pt
Priority to EA200801533A priority patent/EA200801533A1/ru
Priority to CA002635847A priority patent/CA2635847A1/fr
Priority to EP07857476A priority patent/EP1971575B1/fr
Priority to DE502007003499T priority patent/DE502007003499D1/de
Priority to PL07857476T priority patent/PL1971575T3/pl
Priority to US12/159,330 priority patent/US20080318331A1/en
Priority to AT07857476T priority patent/ATE465147T1/de
Priority to JP2009541995A priority patent/JP2010513633A/ja
Publication of WO2008074709A1 publication Critical patent/WO2008074709A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/007—Coloured or dyes-containing lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
    • Y10T436/145555—Hetero-N

Definitions

  • the present invention relates to the use of compounds of general formula (I)
  • X, Y independently of one another, same or different, O, NR 4 ,
  • a 1 B independently of one another, same or different, O, NR 5 ,
  • R 1 , R 2 independently of one another, the same or different, H,
  • Ci-C 2 O-AlkVl C 2 -C 2 o-alkenyl, C 2 -C 20 -alkynyl, Cs-ds-cycloalkyl,
  • R4 is H, Ci-C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 -alkyl kinyl, C3-Ci5-cycloalkyl, aryl, heterocycles
  • R5 is H, Ci-C 2 -alkyl, C 2 -C 2 -alkenyl, C 2 -C 20 -alkyl kinyl,
  • R 6 , R 7 , R 8 , R 9 independently of one another, identical or different, H, C 1 -C 20 -alkyl, C 1 -C 20 -alkylcarbonyl, C 1 -C 20 -alkoxy, C 1 -C 20 -
  • substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 or R 9 may each be interrupted at any position by one or more heteroatoms, wherein the number of these heteroatoms is not more than 10, preferably not more than 8, very particularly preferably not more than 5 and in particular not more than 3, and / or in any position, but not more than five times, preferably not more than four times and particularly preferably not more than three times, by NR 1 R 2, CONR 1 R 2, COOM, COOR 1, SO 3 M, SO 3 R 1, CN, NO 2, C 20 alkyl, C 20 alkoxy, aryl, aryloxy, heterocycles, Heteroatoms or halogen may be substituted, which may also be substituted at most twice, preferably at most once substituted with said groups.
  • the invention further relates to liquids containing a compound of general formula (I) as a marker. Furthermore, the invention relates to methods for the detection of markers in liquids and for the identification of liquids, which contain at least one compound of the general formula (I). Furthermore, the invention relates to various novel compounds of general formula (I).
  • EP 1 001 003 A1 describes a process for the invisible marking of mineral oil products with the aid of dyes. These dyes may, inter alia, also be certain 1,4-substituted anthraquinone derivatives which, however, do not include compounds of the general formula (I).
  • the publications EP 1 323 81 1 A2, EP 1 422 284 A2, EP 1 426 434 A2, EP 1 479 749 A1 and EP 1 486 554 A1 disclose methods for marking mineral oils by adding various anthraquinone derivatives.
  • WO 2005/063942 A1 discloses fuel and lubricant concentrates which contain at least one anthraquinone derivative as a marker. Compounds of the general formula (I) are not described as markers.
  • anthraquinonedicarboximides in particular specific anthraquinonedicarboximides (“anthraquinonedicarboximides”) and processes for their preparation are known.
  • DE 939 044 and DE 945 112 describe processes for the preparation of imidazole-substituted 1, 4-diamino-2,3-anthraquinonedicarboximides and their use in the dyeing of polyethylene terephthalic acid ester fibers. A use of these compounds as markers for liquids is not disclosed.
  • DE 1 176 777 describes the preparation of certain anthraquinonedicarboxylic acid imides starting from 1-amino-4-nitroanthraquinone-2-carboxylic acid. A use of these compounds as markers for liquids is not disclosed.
  • Detection of the tags often occurs by spectroscopic methods by detection of absorbance or fluorescence.
  • a further object of the invention was therefore to find markers which are one with respect to the known ones Marking substances, in particular the anthraquinones used for the marking of mineral oils, increased quantum yield.
  • the detection of the markers can be done at different temperatures. It is therefore necessary to find markers whose detection can be carried out as temperature-independent as possible or with reproducible known temperature dependence.
  • anthraquinonedicarboximides and related compounds both have good solubility and very good long-term stability, in particular over conventional fuel additives. Furthermore, anthraquinone dicarboximides which fall under the above-described compounds of the general formula (I) are distinguished, in particular, by an increased fluorescence quantum yield compared with the anthraquinone derivatives used as mineral oil markers in the prior art. The found temperature dependence of the fluorescence is often very low in the compounds of general formula (I).
  • Terms of the form C 3 -Cb in the context of this invention designate chemical compounds or substituents with a certain number of carbon atoms.
  • the number of carbon atoms can be selected from the entire range from a to b, including a and b, a is at least 1 and b is always greater than a.
  • Further specification of the chemical compounds or substituents is made by terms of the form C 3 -Cb-V.
  • V stands for a chemical compound class or substituent class, for example for alkyl compounds or alkyl substituents.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.
  • Alkali metals are Li, Na or K.
  • the alkali metals (M) in the chemical group -SO3M or -COOM can occur as monovalent positively charged ions.
  • C 1 -C 20 -alkyl straight-chain or branched hydrocarbon radicals having up to 20 carbon atoms, for example C 1 -C 10 -alkyl or C 2 -C 20 -alkyl, preferably C 1 -C 10 -alkyl, for example C 1 -C 3 -alkyl, such as methyl, ethyl, propyl , Isopropyl, or C 4 -C 6 -alkyl, n-butyl, sec-butyl, tert-butyl, 1, 1-dimethylethyl, pentyl, 2-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2 -Dimethylpropyl, 1-ethylpropyl, hexyl, 2-methylpentyl, 3-methyl-pentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethyl
  • Trimethylpropyl 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, or C 7 -C 10 -alkyl such as heptyl, octyl, 2-ethyl-hexyl, 2,4 , 4-trimethylpentyl, 1, 1, 3,3-tetramethylbutyl, nonyl or decyl and their isomers.
  • C 1 -C 20 -alkylcarbonyl a straight-chain or branched alkyl group having 1 to 20 carbon atoms (as mentioned above) which is attached via a carbonyl group (-CO-), preferably C 1 -C 10 -alkylcarbonyl, such as, for example, formyl, acetyl, n- or iso Propionyl, n-, iso-, sec- or tert-butanoyl, n-iso-, sec- or tert-pentanoyl, n- or iso-nonanoyl, n-dodecanoyl.
  • -CO- carbonyl group
  • C 1 -C 20 -alkoxy denotes a straight-chain or branched alkyl group having 1 to 20 carbon atoms (as mentioned above) which are attached via an oxygen atom (-O-), for example C 1 -C 10 -alkoxy or C 2 -C 20 -alkoxy, preferably C 1 -C 20 -alkoxy.
  • Ci-C2o-alkoxycarbonyl is an alkoxy group having 1 to 20 carbon atoms (as mentioned above), which is attached via a carbonyl group (-CO-), preferably C-i-do-alkyloxycarbonyl.
  • C 2 -C 20 -alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 20 carbon atoms and one double bond in any position, for example C 2 -C 10 -alkenyl or C 2 -C 20 -alkenyl, preferably C 2 -C 10 -alkenyl, such as C 2 -C 4 -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl 2-propenyl, 2-methyl-2-propenyl, or Cs-C ⁇ -alkenyl, such as 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl 1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl
  • C 2 -C 20 -alkenylcarbonyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 20 carbon atoms and a double bond in any position (as mentioned above) which are attached via a carbonyl group (-CO-), preferably C 2 -C 10 -alkylcarbonyl such as, for example Ethenyl, propenoyl, butenoyl, pentenoyl, nonenoyl and their isomers.
  • C 2 -C 20 -alkynyl straight-chain or branched hydrocarbon groups having 2 to 20 carbon atoms and a triple bond in any position, for example C 2 -C 10 -alkynyl or C 2 -C 20 -alkynyl, preferably C 2 -C 10 -alkynyl, such as C 2 -C 4 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, or C 5 -C 7 -alkynyl, such as 1-pentynyl, 2-pentynyl , 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2
  • C 2 -C 20 -alkynylcarbonyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 20 carbon atoms and a triple bond in any position (as mentioned above) which are attached via a carbonyl group (-CO-), preferably C 2 -C 10 -alkynylcarbonyl such as, for example Propinoyl, butinoyl, pentanoyl, noninoyl, decinoyl and their isomers.
  • C3-C15-cycloalkyl monocyclic, saturated hydrocarbon groups having 3 to 15 carbon ring members, preferably Cs-Cs-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl and a saturated or unsaturated cyclic system such as. B. norbornyl or norbenyl.
  • C 3 -C 15 -cycloalkylcarbonyl monocyclic, saturated hydrocarbon groups having 3 to 15 carbon ring members (as mentioned above) which are attached via a carbonyl group (-CO-), preferably Cs-Cs-cycloalkylcarbonyl.
  • Aryl a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, e.g. As phenyl, naphthyl or anthracenyl, preferably a mono- to binuclear, more preferably a mononuclear aromatic ring system.
  • Arylcarbonyl preferably a mono- to trinuclear aromatic ring system (as mentioned above) which is attached via a carbonyl group (-CO-), such as.
  • B. benzoyl preferably a mono- to binuclear, more preferably a mononuclear aromatic ring system.
  • Aryloxy is a mono- to trinuclear aromatic ring system (as mentioned above) which is attached via an oxygen atom (-O-), preferably a mono- to binuclear, particularly preferably a mononuclear aromatic ring system.
  • Aryloxycarbonyl is a mono- to trinuclear aryloxy group (as mentioned above) which is attached via a carbonyl group (-CO-), preferably a mononuclear to dinuclear, more preferably a mononuclear aryloxycarbonyl.
  • Heterocycles five- to twelve-membered, preferably five- to nine-membered, particularly preferably five- to six-membered, oxygen, nitrogen and / or sulfur atoms, optionally multi-ring systems such as furyl, thiophenyl, pyrryl, Pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxy, benzimidazolyl, benzothiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyrryl, methoxyfuryl, dimethoxypyridyl, difluoropyridyl, methylthiophenyl, isopropylthiophenyl or part. -Butylthiophenyl.
  • the heterocycles may be chemically attached in any manner to the compounds of the general formula (I), for example via a bond to a carbon atom of the heterocycle or a bond to one of the heteroatoms.
  • five- or six-membered saturated nitrogen-containing ring systems which are attached via a ring nitrogen atom and which may contain one or two further nitrogen atoms or another oxygen or sulfur atom.
  • R 1 C 1 -C 20 -alkyl or aryl).
  • COOM represents salts of carboxylic acids (for example monovalent alkali metal salts).
  • Ci-C 2 O-AIkVl or aryl Ci-C 2 O-AIkVl or aryl
  • SO3M represents salts of sulfonic acids (for example monovalent alkali metal salts).
  • CONR 1 R 2 represents optionally substituted carboxylic acid amides.
  • R 1 and R 2 are identical or different and are C 1 -C 20 -alkyl or aryl.
  • Heteroatoms are phosphorus, oxygen, nitrogen or sulfur, preferably oxygen, nitrogen or sulfur.
  • the symbols in formula (I) preferably have the following meaning:
  • X, Y independently of one another, same or different, O, NR 4 ,
  • A, B independently of one another, identical or different, NH, O, R 1 , R 2 are identical or different and are H, C 1 -C 20 -alkyl, aryl,
  • R 3 is C 1 -C 2 -alkyl, C 3 -C 5 -cycloalkyl, aryl, heterocycles,
  • R 4 H, C 1 -C 2 -alkyl, aryl, heterocycles,
  • R 6 , R 7 , R 8 , R 9 independently of one another, the same or different, H,
  • A, B independently of one another, identical or different, NH, O, R 1 , R 2 H,
  • R 3 is C 1 -C 20 -alkyl, C 3 -C 5 -cycloalkyl, aryl,
  • R 6 , R 7 , R 8 , R 9 independently of one another, the same or different, H,
  • R 6 , R 7 , R 8 , R 9 are each independently, identically or differently, H, C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy, aryl, aryloxy, NR 1 R 2 , F, Cl, Br, CN .
  • both individual compounds of the general formula (I) or mixtures of compounds of the general formula (I) can be used in the process according to the invention.
  • the compounds of the general formula (I) can be prepared by methods familiar to the person skilled in the art, as described, for example, in M. C. Marschalk, Bull. Soc. Chim. 1937, 184-193, DE 1 769 470, DE 1 176 777, DE 939 044 and DE 945 1 12 are described.
  • the invention therefore also relates, inter alia, to compounds of the general formula (I) in which the symbols in the formula (I) have the following meanings: X 1 Y NH,
  • R 3 is C 1 -C 20 -alkyl, R 6 , R 7 , R 8 , R 9 H.
  • the compound with R 3 Ci3-alkyl: i ⁇ -Diamino-N-tridecyl ⁇ - anthraquinonedicarboximide.
  • the tridecyl substituent in this compound may also be an isomeric mixture of various tridecyls.
  • the dodecyl substituent in the compound 1,4-diamino-N- (4-dodecylphenyl) -2,3-anthraquinonedicarboximide may of course also be a mixture of isomers of various dodecyls.
  • Suitable liquids which can be labeled by means of the compounds of the general formula (I) according to the process according to the invention are in particular water or organic liquids, for example alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, pentanol, Isopentanol, neopentanol or hexanol, glycols, such as 1, 2-ethylene glycol, 1, 2 or 1, 3 Propylene glycol, 1,2,3,3 or 1,4-butylene glycol, di- or triethylene glycol or di- or tripropylene glycol, ethers, such as methyl tert-butyl ether, 1,2-ethylene glycol mono- or dimethyl ether, 1, 2-ethylene glycol mono- or diethyl ether, 3-methoxypropanol, 3-isopropoxypropanol, tetrahydrofuran or dioxane, ketones, such as
  • the invention furthermore relates to liquids, preferably oils, in particular mineral oils, which contain at least one compound of the general formula (I) as a marker.
  • the compounds of the general formula (I) which are to be used as markers are added to the liquids in quantities such that a reliable detection is ensured.
  • the (weight related) total content amounts to Markers in the labeled liquid about 0.1 to 5000 ppb, preferably 1 to 2000 ppb and more preferably 1 to 1000 ppb.
  • the compounds are generally added in the form of solutions (stock solutions).
  • suitable solvents for preparing these stock solutions are preferably aromatic hydrocarbons, such as toluene, xylene or higher-boiling aromatic mixtures.
  • a total concentration of the markers of from 0.5 to 50% by weight, preferably 0.5 to 40% by weight, is generally selected. particularly preferably, 0.5 to 30 wt .-% based on the total weight of these stock solutions.
  • the compounds of the general formula (I) can also be used in admixture with other markers / dyes.
  • the total amount of the markers in the liquids is then usually in the range described above.
  • the invention also provides a process for the marking of liquids, preferably oils, in particular mineral oils, wherein the liquid is a compound of general formula (I) is added.
  • the invention also provides a method for the detection of markers in liquids containing at least one compound of general formula (I).
  • the detection of the compounds of the general formula (I) in the liquids is carried out by conventional methods known to the person skilled in the art. Since the compounds of the general formula (I) generally have a high absorption capacity and / or show high fluorescence quantum yield, in the given case, for example, a spectroscopic detection.
  • WO 94/02570 page 14, lines 10-46 and Figure 1
  • WO 99/55805 page 22, line 7 - page 34
  • Z. 46 and WO 99/56125 (p.22, Z. 22 - p. 46, Z. 15).
  • the compounds of the general formula (I) generally have their absorption maximum in the range from 500 to 900 nm and / or fluoresce in the range from 500 to 1000 nm and can thus easily be detected with suitable instruments.
  • the detection can be carried out in a manner known per se, for example by measuring the absorption spectrum of the liquids to be examined.
  • ⁇ ma ⁇ means the wavelength of the longest wavelength absorption maximum of the marker.
  • the wavelength of the maximum emission is usually in the range of 500 to 900 nm.
  • the fluorescent light thus generated is advantageously detected with a semiconductor detector, in particular with a silicon photodiode or a germanium photodiode.
  • Detection is particularly advantageous when there is an interference filter and / or an edge filter (with a short-wave transmission edge in the range from ⁇ max to ⁇ max +80 nm) in front of the detector and / or a polarizer.
  • a preferred method of detecting labels in liquids containing at least one compound of general formula (I) in an amount sufficient to induce detectable fluorescence when irradiated with radiation of a suitable wavelength is carried out by: a) subjecting the liquid to Electromagnetic radiation of a wavelength of 500 to 900 nm is irradiated and b) the excited fluorescence radiation is detected with a device for detecting radiation in the range of 500 to 1000 nm.
  • Another preferred method of detecting labels in liquids containing at least one compound of general formula (I) in an amount sufficient to exhibit detectable absorption upon irradiation with radiation of a suitable wavelength is carried out by: a) Liquid is irradiated with electromagnetic radiation having a wavelength of 500 to 900 nm and b) the absorption of the radiation a) is detected with a device for detecting radiation in the range of 500 to 900 nm.
  • the invention also provides a process for the identification of liquids, preferably oils, in particular mineral oils, which contain a compound of the general formula (I) in an amount which is sufficient to excite a detectable fluorescence upon irradiation with a suitable wavelength, where a) the liquid with electromagnetic radiation of a wavelength of
  • the absorption of the electromagnetic radiation a) is detected with a device for detecting radiation and c) the excited fluorescence radiation is detected with a device for detecting radiation in the range from 500 to 900 nm and d) the liquid is identified by means of the absorption b) and / or fluorescence c) and e) the concentration of the compound of the general formula (I) in the liquid is determined with the aid of the fluorescence radiation c).
  • the measurement data from steps b) and e) of the method are linked in order to carry out the identification.
  • the identification may contain as a further step the comparison with known spectroscopic data.
  • the known spectroscopic data are electronically stored spectra which can be stored, for example, in data beacons.
  • the wavelength positions of the absorption maxima ⁇ ma ⁇ preferably differ by a spectroscopically measurable amount.
  • the layers of the absorption maxima preferably each differ by the amount of at least 40 nm.
  • ⁇ max in this case means the wavelength of the longest wavelength absorption maximum of the marking substance.
  • the absorption bands of the compounds of general formula (I) may either overlap or be separate from each other.
  • targeted detection and the combined detection of several spectroscopic properties, for example in absorption or fluorescence so-called “fingerprint systems” can be built up in the inventive use of mixtures of the compounds of general formula (I).
  • the absorption bands of the labels (MA) and the compounds of general formula (I) may either overlap or be separate.
  • targeted detection and the combined detection of several spectroscopic properties, for example in absorption or fluorescence, can be built up in the inventive use of mixtures of the marking substances (MA) and the compounds of general formula (I) so-called "fingerprint systems".
  • the quantitative ratio of markers (MA) to compounds of general formula (I) is generally dependent on the particular application and the detection sensitivity of the marker (MA).
  • the respective proportions can be determined by the expert on the basis of simple routine tests for the respective application.
  • marker substances mention may be made of the compounds of the general formula (I) of different anthraquinones, phthalocyanines (metal-free and metal-containing) or naphthalocyanines. Preference is given by the compounds of the general general formula (I) various anthraquinones or phthalocyanines and particularly preferably phthalocyanines used.
  • the compounds of the general formula (I) can also be used as a component in additive concentrates (hereinafter also referred to as "packagings"), which in addition to a carrier oil and a mixture of different fuel additives generally also include dyes as well as, for the invisible fiscal or manufacturer-specific marking, additionally contain markers.
  • packages allow various mineral oil distribution companies to supply themselves from a “pool” of unadditized mineral oil and only with the help of their individual packages to supply the mineral oil, e.g. during filling into appropriate transport containers, which give company-specific additives, colouration and marking.
  • Such packages according to the invention then contain as components in particular: a) at least one compound of the general formula (I), b) at least one carrier oil, c) at least one additive selected from the group consisting of i. Detergents, ii. Dispersants and iii. Valve seat wear-inhibiting additives, d) and optionally further additives and auxiliaries.
  • the carrier oils used are usually viscous, high-boiling and, in particular, thermostable liquids. They coat the hot metal surfaces, eg. As the inlet valves, with a thin film of liquid and prevent or delay thereby the formation and deposition of decomposition products on the metal surfaces.
  • base oils mineral carrier oils
  • synthetic carrier oils based on olefin polymers with MN 400 to 1800
  • polybutene or polyisobutene hydrochloride
  • polyalphaolefins or polyinteralalefins synthetic carrier oils based on alkoxylated long-chain alcohols or phenols.
  • Adducts of ethylene oxide, propylene oxide and / or butylene oxide to polybutyl or polyisobutene alcohols to be used as carrier oils are described, for example, in document EP 277 345 A1, further polyalkene alcohol polyalkoxylates to be used in WO 00/50543 A1.
  • Other carrier oils to be used are also polyalkene alcohol-polyetheramines, as listed in WO 00/61708.
  • Carburettors and intake systems of internal combustion engines, but also injection systems for fuel metering, are increasingly burdened by impurities caused, for example, by dust particles from the air and unburned hydrocarbon radicals from the combustion chamber.
  • additives for keeping valves and carburettors or injection systems clean are added to the fuel.
  • Such detergents are generally used in combination with one or more carrier oils.
  • the carrier oils exert an additional "washing function", often assist and promote the detergents in their cleansing and pure-preserving action and can thus contribute to the reduction of the required amount of detergents.
  • carrier oils with detergent / dispersant effect are set out, for example, in the last-mentioned WO document.
  • detergents which are used in the packages are listed, for example, in the publications WO 00/50543 A1 and WO 00/61708 A1 and comprise: Polyisobuteneamines, which are obtainable according to EP-A 244 616 by hydroformylation of highly reactive polyisobutene and subsequent reductive amination with ammonia, monoamines or polyamines, such as dimethyleneaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine,
  • Poly (iso) buteneamines which are obtainable by chlorination of polybutenes or polyisobutenes having double bonds predominantly in the ⁇ and ⁇ position and subsequent amination with ammonia, monoamines or the abovementioned polyamines,
  • Polyisobuteneamines which are obtainable according to DE-A 196 20 262 from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols,
  • Polyetheramines which are prepared by reacting C 2 -C 30 -alkanols, C 6 -C 50 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols with from 1 to 30 mol of ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl or amino group and subsequent reductive amination with ammonia, monoamines or the abovementioned polyamines are obtainable, and
  • Polyisobutene Mannich bases which are obtainable according to EP-A 831 141 by reacting polyisobutene-substituted phenols with aldehydes and monoamines or the abovementioned polyamines.
  • detergents and / or valve seat wear-inhibiting additives to be used are listed, for example, in the document WO 00/47698 A1 and comprise compounds which have at least one hydrophobic hydrocarbon radical having a number-average molecular weight (MN) of from 85 to 20 000 and at least one polar grouping, and which are selected from:
  • polyoxy-C 2 -C 4 -alkylene groups terminated by hydroxyl groups, mono- or polyamino groups, wherein at least one nitrogen atom has basic properties, or terminated by carbamate groups,
  • monoamino groups (i) containing additives are those from polyisobutene epoxides by reaction with amines and subsequent dehydration and Reduction of the amino alcohols obtainable compounds, as described in particular in the document DE 196 20 262 A1.
  • These reaction products typically are mixtures of pure nitropolyisobutanes (e.g., ⁇ , ⁇ -dinitropolyisobutane) and mixed hydroxynitropolyisobutanes (e.g., ⁇ -nitro- ⁇ -hydroxy polyisobutane).
  • Carboxyl groups or their alkali metal or alkaline earth metal salts (iv) containing additives are preferably copolymers of C2-C4o-olefins with maleic anhydride having a total molecular weight of 500 to 20,000 whose carboxyl groups wholly or partially to the alkali metal or alkaline earth metal salts and a remainder of the Carboxyl groups are reacted with alcohols or amines.
  • Such additives are known in particular from document EP 307 815 A1.
  • Such additives are primarily for preventing valve seat wear and may, as in the Scriptures WO 87/01 126 A1, with advantage in combination with conventional detergents, such as poly (iso) butenamines or polyetheramines used.
  • Sulfonic acid groups or their alkali metal or alkaline earth metal salts (v) containing additives are preferably alkali metal or alkaline earth metal salts of a Sulfobern- steinklaklalesters, as described in particular in EP 639 632 A1.
  • Such additives serve primarily to prevent valve seat wear and can be used to advantage in combination with conventional detergents such as poly (iso) buteneamines or polyetheramines.
  • Polyoxy-C2-C4-alkylene (vi) containing additives are preferably polyether or polyetheramines, which by reaction of C2-C6o-alkanols, C6-C30alkanediols, mono- or di-C2-C3o-alkylamines, Ci-C3o Alkylcyclohexanols or C 1 -C 30 -alkylphenols with 1 to 30 mol of ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of the polyetheramines, by subsequent reductive amination with ammonia, monoamines or polyamines nen are available.
  • Such products are described in particular in EP 310 875 A1, EP 356 725 A1, EP 700 985 A1 and US Pat. No. 4,877,416.
  • polyethers such products also meet carrier oil properties. Typical examples are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates, and the corresponding reaction products with ammonia.
  • Carboxyl ester groups (vii) containing additives are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, especially those having a minimum viscosity of 2 mm2 / s at 100oC, as described in particular in DE 38 38 918 A1.
  • mono-, di- or tricarboxylic acids it is possible to use aliphatic or aromatic acids; as ester alcohols or polyols, especially long-chain representatives having, for example, 6 to 24 carbon atoms are suitable.
  • Typical representatives of the esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of iso-octanol, iso-nonanol, iso-decanol and iso-tride.
  • Mannich reaction of phenolic hydroxyl groups with aldehydes and mono- or polyamines generated groupings (ix) containing additives are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine.
  • Such "polyisobutene-Mannich bases” are described in particular in document EP 831 141 A1.
  • Dispersants as component c) are, for example, imides, amides, esters and ammonium and alkali metal salts of polyisobutene succinic anhydrides. These compounds find particular use in lubricating oils, but in some cases also as detergents in fuel compositions.
  • organic solvents for example alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, pentanol, isopentanol, neopentanol or hexanol
  • glycols such as 1, 2-ethylene glycol, 1, 2 or 1, 3-propylene glycol, 1, 2, 2,3 or 1,4-butylene glycol, di- or triethylene glycol or di- or tripropylene glycol
  • ethers such as methyl tert-butyl ether, 1,2-ethylene glycol mono- or dimethyl ether, 1, 2-ethylene glycol mono- or diethyl ether, 3-methoxypropanol, 3-isopropoxypropanol, tetrahydrofuran or dioxane
  • ketones such as acetone, methyl ethyl ketone or diacetone alcohol
  • esters such as methyl methyl ethyl ketone
  • Corrosion inhibitors for example based on film-forming ammonium salts of organic carboxylic acids or of heterocyclic aromatics in non-ferrous metal corrosion protection,
  • Antioxidants or stabilizers for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or of phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid,
  • Metallocenes such as ferrocene or methylcyclopentadienyl manganese tricarbonyl,
  • Lubricity additives such as certain fatty acids, alkenylsuccinic acid esters, bis (hydroxyalkyl) fatty amines, hydroxyacetamides or castor oil,
  • the concentration of component a), i. the at least one compound of the general formula (I) in the packages according to the invention is usually selected at a level such that after addition of the package to the mineral oil the desired concentration of marking substance (s) is contained therein.
  • Typical concentrations of the markers in the mineral oil are approximately in the range of 0.01 to a few 10 ppm by weight.
  • Component b) i. the at least one carrier oil is usually in the packages in a concentration of 1 to 50, in particular 5 to 30 wt .-%, and component c), i. the at least one detergent and / or the at least one dispersant, usually in a concentration of 25 to 90 wt .-%, in particular 30 to 80 wt .-%, in each case based on the total amount of components a) to c) and optionally d), wherein the sum of the individual concentrations of the components a) to c) and optionally d) to 100 wt .-% complements.
  • corrosion inhibitors for lowering the pH of the fuel are contained in the packages, their total concentration usually amounts to not more than 10% by weight. - %, based on the total amount of the package (ie the total amount of components a) to c) and d)), wherein the concentration of the corrosion inhibitors and demulsifiers usually in the range of about 0.01 to 0.5 wt .-% the total amount of the package.
  • organic solvents are contained in the packages, their concentration in the sum usually amounts to not more than 20 wt .-%, based on the total amount of the package.
  • these solvents are obtained from solutions of the markers and / or dyes which are added to the packages with a view to a more precise meterability instead of the pure markers and / or dyes.
  • component d If, as component d), other markers other than the compounds of the general formula (I) are contained in the packages, their concentration is again measured at the content which they should have after addition of the packages in the mineral oil. The same applies to component a).
  • dyes are present in the packages according to the invention as component d), their concentration is usually about between 0.1 to 5 wt .-%, based on the total amount of the package.
  • Tridecylamine isomer mixture Sales product of BASF Aktiengesellschaft.
  • reaction mixture was reheated to 120 0 C and held at this temperature for about 3.5 h. This was followed by another addition of 2.0 g (0.01 mol) of tridecylamine isomer mixture. After a further 17.5 h at 120 ° C., the reaction mixture was cooled to room temperature and filtered, leaving behind a solid, which was washed and dried in a vacuum drying oven. From the filtrate was added by adding about 200 ml Methanol further solid precipitated, which was filtered off, washed and dried in a vacuum oven cupboard.
  • the marker 4-diamino-N-isopropyl-2,3-anthraquinonedicarboximide
  • the solution of the marker was excited by means of a laser diode having a power of 3 mW and an excitation wavelength of 660 nm.
  • the fluorescence was perpendicular to the excitation beam through a commercial edge filter with a Kan ten wavelength of 695 nm (long pass) integrally detected by Si photodiode.
  • Example 3 Detection of a marker by detection of fluorescence in gasoline
  • Example 1 The marker of Example 1 was dissolved in ARAL® Ultimate brand gasoline. The following results for the fluorescence intensities were obtained:
  • the fluorescence signal correlates linearly well with the concentration.
  • the square of the correlation coefficient is: 0.995.
  • the markers were dissolved in methylene chloride (MCL) and the longest wavelength

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Materials By Optical Means (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne l'utilisation de composés de formule générale (I) en tant que marqueurs pour liquides, un procédé de détection de marqueurs dans des liquides, un procédé d'identification de liquides et un composé sélectionné de formule générale (I).
PCT/EP2007/063813 2006-12-20 2007-12-12 Dérivés d'anthraquinone en tant que marqueurs pour liquides WO2008074709A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
AU2007336381A AU2007336381A1 (en) 2006-12-20 2007-12-12 Anthraquinone derivatives as markers for liquids
BRPI0706749-6A BRPI0706749A2 (pt) 2006-12-20 2007-12-12 uso de compostos, lìquido, métodos para detectar marcadores em lìquidos, e para identificar lìquidos, e, composto
EA200801533A EA200801533A1 (ru) 2006-12-20 2007-12-12 Производные антрахинона в качестве маркирующих веществ для жидкостей
CA002635847A CA2635847A1 (fr) 2006-12-20 2007-12-12 Derives d'anthraquinone en tant que marqueurs pour liquides
EP07857476A EP1971575B1 (fr) 2006-12-20 2007-12-12 Dérivés d'anthraquinone en tant que marqueurs pour liquides
DE502007003499T DE502007003499D1 (de) 2006-12-20 2007-12-12 Anthrachinonderivate als markierstoffe für flüssigkeiten
PL07857476T PL1971575T3 (pl) 2006-12-20 2007-12-12 Pochodne antrachinonu jako znaczniki dla cieczy
US12/159,330 US20080318331A1 (en) 2006-12-20 2007-12-12 Anthraquinone Derivatives as Markers For Liquids
AT07857476T ATE465147T1 (de) 2006-12-20 2007-12-12 Anthrachinonderivate als markierstoffe für flüssigkeiten
JP2009541995A JP2010513633A (ja) 2006-12-20 2007-12-12 液体用マーカーとしてのアントラキノン誘導体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06126725 2006-12-20
EP06126725.8 2006-12-20

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WO2008074709A1 true WO2008074709A1 (fr) 2008-06-26

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CL (1) CL2007003707A1 (fr)
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JP2010523751A (ja) * 2007-04-05 2010-07-15 ビーエーエスエフ ソシエタス・ヨーロピア シリコンおよびゲルマニウムフタロシアニンならびに関連物質の製造
JP6989279B2 (ja) * 2017-04-20 2022-01-05 日本化薬株式会社 アンスラキノン系化合物及び染色方法
JP6989278B2 (ja) * 2017-04-20 2022-01-05 日本化薬株式会社 アンスラキノン系化合物及び染色方法
BR112021017902A2 (pt) * 2019-03-11 2021-12-07 Nippon Kayaku Kk Tinta de impressão para impressão dos tecidos e método de impressão dos tecidos em fibra

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1001003A1 (fr) * 1998-11-09 2000-05-17 Morton International, Inc. Methode de marquage invisible de produits pétroliers au moyen de colorants visibles
EP1479749A1 (fr) * 2003-05-23 2004-11-24 Rohm and Haas Company Procédé de marquage des hydrocarbures liquides dérivés du pétrole
EP1486554A1 (fr) * 2003-06-13 2004-12-15 Rohm and Haas Company Procédé de marquage des hydrocarbures avec des anthraquinones

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US328274A (en) * 1885-10-13 Machine
US348114A (en) * 1886-08-24 Thomas a
US2628963A (en) * 1951-12-05 1953-02-17 Du Pont 1,4-diamino-2,3-anthraquinone-dicarboximides
US2753356A (en) * 1952-01-25 1956-07-03 Du Pont 1, 4-diamino-2, 3-anthraquinone-dicarboximides
US3164449A (en) * 1961-03-01 1965-01-05 Du Pont Anthraquinone dyes for gasoline
DE10361504A1 (de) * 2003-12-23 2005-07-28 Basf Ag Kraft- und Schmierstoffadditiv-Konzentrate, enthaltend mindestens ein Anthrachinon-derivat als Markierungsstoff

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1001003A1 (fr) * 1998-11-09 2000-05-17 Morton International, Inc. Methode de marquage invisible de produits pétroliers au moyen de colorants visibles
EP1479749A1 (fr) * 2003-05-23 2004-11-24 Rohm and Haas Company Procédé de marquage des hydrocarbures liquides dérivés du pétrole
EP1486554A1 (fr) * 2003-06-13 2004-12-15 Rohm and Haas Company Procédé de marquage des hydrocarbures avec des anthraquinones

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EP1971575B1 (fr) 2010-04-21
BRPI0706749A2 (pt) 2011-04-05
AR064467A1 (es) 2009-04-01
UA89463C2 (ru) 2010-01-25
EA200801533A1 (ru) 2008-12-30
EP1971575A1 (fr) 2008-09-24
ZA200805635B (en) 2009-11-25
CL2007003707A1 (es) 2008-04-11
CA2635847A1 (fr) 2008-06-26
US20080318331A1 (en) 2008-12-25
JP2010513633A (ja) 2010-04-30
DE502007003499D1 (de) 2010-06-02
AU2007336381A1 (en) 2008-06-26
KR20090101812A (ko) 2009-09-29
ES2343600T3 (es) 2010-08-04
ATE465147T1 (de) 2010-05-15
TW200838849A (en) 2008-10-01
CN101374809A (zh) 2009-02-25
PT1971575E (pt) 2010-06-01
PE20081243A1 (es) 2008-11-14

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